Yarn conditioning process and compositions therefor



Patented Sept. 16, 1941 2,256,381 FlCE A YARN CONDITIONING PROCESS AND COMPOSITIONS THEREFOR Joseph B. Dickey, Rochester, N Y., assignor-to Eastman. Kodak Company, Rochester corporation of New Jersey Application September Serial-No. 3 58,291

' No Drawing.

, N. Y., a

'16 Claims. (c 28-4) This invention relates to the conditioning of textile yarns, and particularly to the conditioning of yarns, threads, filaments and fibers composed of or containing organic derivatives of cellulose such as cellulose acetate, cellulose acetate propionate and cellulose acetate butyrate, to render such materials amenable to various textile operations such as knitting, weaving, carding,.spinning, twisting and the like.

As is well known in the textile industry, the manufacture, processing and use of yarns com-'. posed of or containing organic derivatives of cellulose and similar synthetic materials give rise to numerous problems generally absent from the handling of natural yarns such as silk, wool cottors. and the like. One of the chief problems encountered in dealing with these synthetic materials is to so lubricate or soften and, in some instances, to both lubricate and soften, the yarn in question that it will have the correct frictional:

characteristics or drag, and the required flexibility for the specific purpose in view. In the handling of continuous filament yarn, for example, it is necessary to condition the material to reduce the tendency towardbreakage of individual filaments when the yarn is subjected to mechanical strains such as are involved in passage of the yarn over rolls, guides, and other parts of the yarn-producing mechanism 'and in twisting, winding, reeling and similar operations. In thecase of yarns intended for use on com-- mereial knitting machinery, it is particularly important that the yarn be soft and pliable in order that it may conform to the contour of the needles and give a closely knit fabric free from cuts, pin holes, stitch distortion, ladderlng, misplaits and other common defects.

Another problem of major proportions presented by these synthetic yarns is their extreme tendency to pick up chargesof static electricity, especially in such operations as twisting, winding", warping, picking, carding, combing, drafting, spinning, and the like. This tendency is particularly aggravated in the case of cut staple fibers, since in the commercial use of such material, itis normally subjected to a number-of extremely severe operations such as picking, carding, combing, etc., all of which tend to so charge the individual fibers as to make proper web formation diificult or impossible or to give the ultimate yarn an undesirable unevenness.

-- conditioning composition, whether primarily designed for use as a warp, filling or knitting lubricant, or as an anti-static, all of the various components and their functions must be delicately balanced one against the other so as to -give a practical and commercially satisfactory yam treatment.

Heretoforc, many different conditioning agents such as polyhydric alcohols and similar compounds have been suggested as ingredients of yarn conditioning formulas, generally-in con- In some types of yarn, all three of the abovementioned problems of lubrication, softening and anti-static treatment are present and in any 'case the matter of providing a yarnconditioning composition, in which the several functions are properly coordinated to accomplish the'desired result is often a matter. of extreme difficulty. Y

general formula:

junction with mineral, vegetable and animal oils. It' has been found in practice, however, that most of these agents and the various formulas containing them have certain drawbacks, among which may be mentioned too drastic solvent action on the yarn, insufliclent solventpo'wer for the lubricants with which they are used and a tendency to form gummy deposits on the yarn after application. Furthermore, many of the known yarn treating agents are insufllciently soluble in water to permit satlsfactoryremoval from the yarn by aqueous scour baths.

The present invention has as its principal ob- I ject to provide an improved process for the conditioning of textile yarns, threads, filaments, and fibers, particularly those composed of or containing organic derivatives of cellulose to render such materials amenable to various textile operwhom and processes, such as mltting, weaving, spinning and the like. A further object is to provide an improved process for the lubrication and softening of such yarn. A still further object is to provide a new class of yarn treating agents and compositions particularly adapted forthe conditioning of yarns composed of or containing organic derivatives of cellulose and readily removable therefrom by the usual aqueous scour baths. A specific object is to provide ,an improved type of cellulose organic derivative yarn amenable to various textile operations including knitting, weaving, and spinning. Other objects will appear hereinafter;

These objects are accomplishedby the following "invention which, in its broader aspects, comprises treating yarns, particularly those composed of or containing organic derivatives of cellulose, such as cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate and similar organic acid esters with esters of alpha, alpha-carboxywfe' difuryl methane having the wherein Band R are substituents selected from I This is due to the fact that in any given yarn coand wlle'reirr-lieand'R are 2 was from alkyl, allgylene,cycioalkyl, aryl and hetero Other examples of conditioning compositions cyclic groups. Of these substituents, the alkyl which may be applied in accordance with my ingroup may be a methyl, ethyl, beta-hydroxy ventlon to yarns intended for a variety oi. purethyl, butyl oleyl, beta hydroxy.beta ethoxy poses such as knitting, weaving, spinning and the ethyl em Likewise, the alkylene group-s may be a like, and especially the preparation of yarns com- 1 1, h L i 11 I1 the mu 3 posed 01. or containing organic derivatives of 2; g fif i g i' i naphtiylg g cellulose, such as cellulose acetate, cellulose acetate propionate, and cellulose acetate butyrate cycloalkyl and heterocyclic groups may be cycloi ti f knit hexyl, hexahydrobenzyl, tetrahydrofuryl, naph and similar der ves or ng purposes are the following: thenyl' Example 3 The method used in preparing these com- Parts pounds is that described in Gazzeta Chimica HC CH Itallana, 67, 312 (1937).

In the following examples and description I have set forth several of the preferred embodiments of my invention, t t are included (Di-bota-methoxy ethylester oi 5,5-dicarboxy-2,2-difuryl methane) merely for purposes of illustration and not as a 60 limitation thereof. Blown olive oil My invention will be more readily understood :0

by reference to several specific examples of typi- Emmp 1e 4 Parts E-o-c-H HC -CH l H IHI Cl AO=C:HFOg g00,m00,m00,m

0 um, o

(Di-beta-ethoxy-beta-ethoxy ethyl ester of 5,5-diearboxyv-2,2-diiuryl pentadecyl methane) cal yam treating procedures carried out in acc 40 cordance therewith. Light mineral oil Example 1 Example 5 -Ho--oH. nc o1r 35 I Parts o"11,,0-oo-e Les,- goo-o"m, 30-011 0 can-om-oc-g -cm- -COCH1C o v o (Dilauryl ester of 5,5'-d carboxy-2,2-difuryl methane) O 0 is applied by means of an apbncator r011 40 (Dlbenzylesteroi 5,5'-dicarboxy-2,2-diiuryl methane) to cellulose acetate continuous filament, d s i 30 signed for knitting purposes in an amount corsperm on responding to 5-25% of the dry weight of the yarn. The yarn so treated is found to be soft Example 6 and pliable and well-adaptedfor knitting. 4 Parts no--oi1 HO-GH Hr-OOHl w Ditetraliydmhlrluryl out; of ifi-dicflboxy-M-dllur'yl methoxy methyl methane) Example 2 a Blown spermoi Aconditioningli dhav the following co I l position: qui mg m 60. Example? W Parts Parts I Ho on .no--' on 7 nc-cn HC-CH cdIi-o-o m-o-o- -CH 1 l z-c-oonoca o H o \/o"-." 4 05- v (mbum m "341ml mum) (Di-When mimuw-aicarbox -w-dimr i methane) A V v I Olive 011' Y -4o on .3: is applied to cellulose acetate yarn as described 70 s lm t d u -.61 2 in Example 1. Assuming the m is to be used Hmenron 73""? 10 i'or mving,1-5% otthecompositiomba'sedupon 01 em dd a the dry weight of the yarn. is deposited. The A nrnlotreatedis'fmmdtobewelladaptedfor ine r a flupeasnllingyarninweavina. I W ater A 7 'noolm-ootm-oc 439.3 b-c-octm-ocinion Example 8 Parts .3 package. Likewise, the lubricant may be'appnea during twisting, winding," crepeing or similar operations. in some cases, the lubricating, and

softening agent may be added to the spinnin solution from which the yarn is to be spun.

The amount oi the compositions applied will, in general, depend upon the purpose for which 7 a the yarn is to be used. For example, if the yarn x The. particular method of application of, the

yarn treating compositions of my invention to the yarn will depend largely upon the nature of the yam and the use for which it is intended. In general, the compositions may be applied by any of the standard procedures such asroll, wick,-

e yarn is in con- L.

bath, or spray application. It tinuous filament iorm, compositions may be applied just as the yarn emerges from the spinning cabinet, .o while passing from package to 75 organic 'derivatiyesoi cellulose such as cellulose" H (Di-crotyl ester of 6,5'-dicarboxy-2,2-diuiryl crotyl methane) 0. Mineral nil '35 Blown neats-ioot olL; 35 Naphthenyl phosphate ethylamine salt 10 Erample 10 1 Parts 11c --cE. HCCH CtHll-08 C-- /C-8OC|H11 0 on; onto 41E: 43H: "C (Dlcyclohexyl ester oi 5,5'-dicarboxy-2,2',-diiuryl cyclohexyl methane) v 40 31cm teaseed o I K 40 Oleyl alcohol 7 20 Example 11 i 'Parts Water.-- ,so e

o 4 Di-bata-hydroxy' ethoxy ethyl-5,5'#dicarboxy-2,2-diinrylmethane) I Water soluble cellulose ester or ether 5 Glycerol acetone a Example 12 is to be employed for knitting, anywhere from 5.-25%, based on the dry weight of the yarn, may be applied. On the other hand, it the yam is' intended for weaving, the amount will generally run from about 1-5%.

In each 0'! the compositions given, the'essential lubricating and softening component is a compound oi the type indicated above. However, as illustrated by the specific examples, such com-. positions may contain other lubricating, and softening agents, to'augment or supplement the efiect of the primary ingredient and thus give the compositions added or improved'properties.

Likewise, solvents, non-solvents, blending agents,

co-solvents, emulsifying agents, dispersing agents and simiiaringredients may be added as circumstances may require to adapt the compositions for I pending upon the particular purpose for which the composition is intended. For example, if it is desired to control the solvent, softening, or other specific action of the conditioning agent per se or of any other ingredient, the amount thereof may be adjusted in accordance with the desired action. I 4

While I have found it convenient to describe my invention with particular reference to the treatmentof yarns composed of orcontaining organic, derivatives oi cellulose, particularly cellulose acetate, the conditioning-agent andcompositions described herein are also applicable to the conditioning of many other types of cellulose derivative yarns, such as those composed of or containing cellulosepropionate, cellulos'ebutyrate, cellulose acetate propionate, cellulose acetate butyrate, the cellulose ethers such as ethyl, methyl and benzyl celluloses, viscose and cuprammoniumcellulose, silk, wool, cotton and other natural andlartificial materials.

The term yarn as .used herein anddn the claims is to be understood as covering single filaments, a plurality/oi filaments associated in- I the form of roving, threads, and the like, either. of high or low twist, composite threads or yarns c'omposedoi' a mixture of natural and artificial filaments, composite threads formed by twisting togethenindividual threads 'or strands'of the same or 'diiiferent natural or artificial materials of the same or diiierent deniers, creped or crimped yarns, and crimpet'l or uncrimped cut advantages. Theiundamental and distinguish ing characteristic of the agentsdescribed herein is their ability to lubricate and soften yams,

particularly those composed of or containing Acetone acetate, and to render them amenable to various textile operations.

As indicated above, these compounds are distinguished by the fact that they have an especial solvent power for a wide variety of mineral, blown and unblown, drying and semi-drying animal and vegetable oils. Furthermore, due to their ready solubility in water, they may be removed from yarns and fabrics by means of the usual aqueous scour baths. 4

In addition to the use of the compounds in question as yarn conditioning agents, they may be employed as plasticizers for various cellulose derivatives such as cellulose nitrate, cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate, and other single and. mixed esters of cellulose.

The compositions resulting from the plasticization of such esters may be usedin the plastic and analogous arts, such as the manufacture of wrapping sheets, photographic film, varnishes,

Di-beta-hydroxy ethyl ester of 5,5'-dicarboxy-2,2'-difuryl phenyl methane 20 Propylene chloride"... 300 Acetone s g 100 Example 20 Parts Cellulose acetate butyrate 100 (Beta-methoxy ethyl-beta-phenoxy-betaethoxy ethyl ester of 2,2'-dlcarboxy5,5'-di[uryl methane) or lacquers and the like. Typical examples of such compositions are the following:

20 Triphenyl thiophosphate 10 Camphnl 1o Ethylene chloride 400 Methanol Example 21 Parts Ethyl cellulose 100 Dibutyl ester of 5,5'-dicarboxy-2,2'-difuryl methyl methane 60 Example 22 Parts Cellulose acetate propionate butyrate 100 I o-c HC--CH ll [1 H g ll C2 l'-?OcC o-oo-ooocim H c=c o( i (Diethyl ester of 2,2'-dicarboxy'5,5'-diiuryl iuryl methane) Triphenyl phosphite 10 ester of 5,5'-dicarboxy-2,2'-difuryl cyclohexyl methane are outstanding in their ability to lubricate and soften yarns composed of or containing organic derivatives of cellulose and render them amenable 'to a wide variety of textile operations, particularly knitting.

' which comprises applying thereto a lubricating Example 13 Parts Cellulose acetate 100 Dibutyl ester of 5,5'-dicarboxy-2,2'-difuryl methyl methane '80 Acetone 400 Example 14 Parts Cellulose acetate 100 Di-beta-methoxy ethyl ester of 5,5'-dicarboky-2,2'-difuryl methane 20 Methanol 100 Anetnna 300 Example 15 g Parts Cellulose acetate 100 Di-beta-ethoxy-beta-ethoxy ethyl ester of 5, 5' dicarboxy 2,2 difuryl pentadecylmethan 30 Ethylene chloride -1 300 Dioxane 100 Example 16 v Parts Cellulose acetate 100 Dibe'nzyl ester' of 5,5'-dicarbo xy-2,2'-difuryl methane 30 Triphenyl phosphate '20 Acetone a 300 Ethyl acetate 1 100 Erample 17 Cellulose acetate propionate 100 Butyl phthalate .g 20

Ditetrahydrofurfuryl ester of 5,5'-dicarboxy-2,2'-difuryl methoxymethyl methane 30 Propylene chloride .L 100 Ethyl lactate What I claim is:

'1. The process of conditioning yarn to render it more amenable to textile operations including knitting, weaving, spinning and the like and softening composition containing as its essential lubricating and softening component an wherein R. and R are substituents selected from wherein R and R are substituents selected from the group consisting .of hydrogen and alkyl, alkvlene, aryl, cycloalkyl and heterocyclic groups and wherein R and R are substituents selectedv 9 from alkyl, alkylene, cycloalkyl, aryl and heterocyclic groups.

2. The process of conditioning yarn composed of or containing organic derivatives of cellulose to render it more amenable-to textile operations 15 including knitting, weaving, spinning and the like which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component an ester of alpha, alpha-carboxy-a',s' difuryl meth- 20 ane having the general formula:

wherein R and R are substituents selected from the group consisting-of hydrogen and alkyl, alkylene, aryl, cycloalkyl and heterocyclic groups, and wherein R and R are substituents selected from alkyl, alkylene, ,cycloalkyl, aryl and heterocyclic groups.

3. The process of conditioning yarn composed of 01' containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning and the like which comprises applying thereto a lubricating and softening composition containing as its-es.- sent a1 lubricating and softening component an ester of alpha, alpha-carboxy-s',a' dlfuryl methane having the general formula: v

the group consisting of hydrogen and alkyl, alkylene, aryl,. cycloalkyl and heterocyclic groups, and wherein R." and R are substituents selected from alkyl, alkylene, cycloalkyl, aryl 5 and heterocyclic groups.

4. The procea-is of conditioning yam composed of or containing cellulose acetate to render it more amenable to textile operations including comprises applying thereto a lubricating and softening composition'containing as its essential lubricating and softening component dilauryl ester of 5,5'-dicarboxy-2,2'-difuryl methane.

5. The" process of conditioning yarn composed m of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, and the'like, which comprises applying thereto .a lubricating and softening composition containing as its essential "lubricating and softening component di-beta- ,methoxy ethyl ester of 5,5'-dicarboxy-2,2"-difuryl methane. f

6. The process of conditioning yarn composed of or containing cellulose acetate to render it7 lubricating and oftening component dicyclohexyl 75 ester of 5,5'-dicarboxy-2,2-difuryl cyclochexyl methane. '7. Textile yarns amenable to textile operations including knitting, weaving, spinning and the like impregnated with a lubricant containing as its essential lubricating and softening component an ester of alpha, alpha-carboxy-s',a' difuryl methane having the general formula:

H- lJ--CH B HC-CH R 0-c0 'd ('L- -CO-O-R' wherein R' and R are substituents selected from the group consisting of hydrogen and alkyl, alkylene, aryl, cycloalkyl and heterocyclic groups, and

wherein R and R are substituents selected from .alkyl, alkylene, cycloalkyl, aryl and heterocyclic groups.

8. Textile yarns composed of or containing organic derivatives of cellulose amenable to textile operations including knitting, weaving, spinning and the like, impregnated with an ester of alpha, alpha-carboxy ufl difuryl methane having the general formula:

- n-c-cn R BIC-CH wherein R and R are substituents selected from t the group consisting of hydrogen and alkyl, alkylene, aryl, cycloalkyl and heterocyclic groups, and wherein R and R are substituents selected from alkyl, alkylene, cycloalkyl, aryl and heterocyclic groups. I

9. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning and. the like, impregnated with a lubricant comprising dilauryl ester of 5,51 -dicarboxy-.2,2'- difuryl methane. T

10. Textile yarns composed of or containin cellulose acetate amenable .to textile operations including knitting, weaving, spinning" and the like,- impregnated with a lubricant comprising di-beta-methoxy ethyl ester of 5,'-dicarb,oxy- 2,2'-difuryl methane.

l'LTextile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning and the like,'impregnated with a lubricant comprising -dlcyclohexyl ester of 5,5-dicarboxy-2,2'-difuryl cyclohexyl methane.

12. A yarn'lubricating and softening composition containing as its essential lubricating and knitting, weaving, spinning and thelike, which a softening component an ester of alpha, alpha- OEI'bOXY-g'm' difuryl methane having the general formulas I wherein R and R are substituents selected from the group consisting of hydrogen and alkyl, alkylene, aryl, ycloalkyl and heterocyclic groups, and wherein R. and 3. are substituents selected from alkyl, alkylene, cycloalkyl, aryl and heterocyclic oups. I 1

1 8. A yarn lubricating and softening composition containing as its essential lubricating and softening component an ester of" alpha, alphacarboxy-aflafldifuryl methane having the general formula: I

H men R1 lac-( in V o o a Y the group consisting of hydrogen and alkyl, alkylene, aryl, cycloalkyl and heterocyclic groups, and

wherein R and R. are substituents selected from alkyl, alkylene, cycloalkyl, aryl and heterocyclic ups.

14. A yam lubricating and softening composition containing as its essential lubricating and softening component dllauryl ester or 5,5'-dicarboxy-2,2'-diiuryl methane.

2,266,381 wherein R and R are substituents selected from- JOSEPH B. mom. 

